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. Author manuscript; available in PMC: 2010 Apr 15.
Published in final edited form as: J Am Chem Soc. 2009 Apr 15;131(14):5054–5055. doi: 10.1021/ja900827p

Table 1.

anti-Diastereoselective aminoallylation of aldehydes via ruthenium catalyzed transfer hydrogenative coupling of N-substituted allenes 1a-1ea

graphic file with name nihms-104933-t0005.jpg
Entry Allene R1 R2 Yield 3a (dr)
1 1a p-Toluenesulfonyl Benzyl 92% (5:1)
2 1b Phthalimido --- 37% (3:1)
3 1c Boc Benzyl 71% (8:1)
4 1d o-Nitrobenzenesulfonyl Benzyl 59% (≥ 20:1)
5 1e p-Nitrobenzenesulfonyl 2,4-Dimethoxybenzyl 91% (≥ 20:1)
a

In all cases, cited yields are of isolated material. See Supporting Information for detailed experimental procedures.